Depends on character for me. I have some formal folks who are always top-fashion, tres chic all the time(like this one decker lady I play), with armor only if it's also fashionable. Sure it might not be the most effective, but well, up to the character.
My main sammy's choices:
On the street, simply a real leather jacket, steel toed combat boots, hardliner gloves in the pocket in case things get ugly, and a pocketknife. Otherwise, no illegal gear but in this world trouble can come up when you least expect it, even if you try to avoid it. Clothing is always a tank top and jeans(secure armor if for some reason he is green-lighted at the time. Which, again, can happen, especially when other party members say the wrong thing at the wrong time

) In the case of a severe green light, the seat of his bike will contain a light pistol. But i typically play runners when on the street with little weaponry. That you can see, anyway. One's body should be all the defense one needs if push comes to shove comes to you can't talk out of it.
On jobs, the list gets more extensive. Here is your basic, garden variety 'run
Black swat mask
Hardline gloves
Armor Vest w/ Plates
Either a Secure Armor Jacket or Urban Camo Full Suit(layered with the vest, its 6/4)
Forearm Guards
Cougar Fineblade Long or Katana(depending)
Heavy pistol in concealed quick draw holster, with a couple extra clips and a silencer
Primary weapon(depends. For heavy but more discreet, a sound supressed Franchi Spas 22 on SA. For bigger bangs, the Enfield with a 50 round drum of APDS.) Carries some stun rounds at either rate.
Survival Knife
pocket flashlight
UV light
Goggles or binoculars(he has all the eye vision enhancements)
the popular snake mesh socks
I also customized the boots he wears(the full height combat boots) with a retractable blade for a nasty surprise if needed.

Of course, tools are brought if needed(he has an electronic tools kit if needed), and also, knows some demolitions, so for big bang jobs, along comes some boom.
Lots of jobs are different tho, some require suits and mingling, some require just a lot of destruction...but the top list is the 'typical' list.